Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment

Abstract

Maillard reaction intermediate (MGX) generated from glutathione and xylose in aqueous medium was prepared via the Maillard reaction performed under a two-stage temperature increase process. The purified MGX was identified by Fourier-transform infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance as N-(1-deoxyd-xylulos-1-yl)-glutathione (Amadori compound, C 15 H 25 O 10 N 3 S) with five main isomers. The method of Maillard reaction performed under a two-stage temperature increase process was further verified by high-performance liquid chromatography. The optimal reaction time and temperature for the preparation of MGX was determined as 60 min at 90°C. The yield of MGX was increased from 8.60% to 55.52% through thermal reaction coupled with vacuum dehydration. In addition, rapid and more Maillard-type volatile compounds were formed in MGX during thermal treatment than that in Maillard reaction products or glutathione-xylose mixture. Beside, MGX possessed more pleasing meat-like volatile profile compared with the Amadori compound of glutamic acid-xylose (AAX), cysteine-xylose (ACX), and glycinexylose (AGX). Therefore, it suggested that the MGX had the potential to achieve a better flavor formation during thermal treatment.Keywords: a 2-stage temperature increase process, Maillard reaction intermediate, Maillard-type volatile formation, N-(1-deoxy-d-xylulos-1-yl)-glutathione, thermal treatmentPractical Application: Maillard reaction intermediates, such as Amadori or Heyns rearrangement products (ARP or HRP), are important flavor precursors, which possess stable physicochemical properties, but tend to degrade into flavor compounds at high temperatures. Maillard reaction intermediate from glutathione and xylose acts as primary flavor enhancers to complete Maillard reaction to produce flavors in the subsequent thermal processing, which can significantly improve and stabilize the flavor quality of the meaty food, and deserves a very broad application prospects. The new developed method will be a significant theoretical basis on research preparation and properties of Maillard reaction intermediates in complex food systems.

Promoted Formation of Pyrazines and Sulfur-Containing Volatile Compounds through Interaction of Extra-Added Glutathione or Its Constituent Amino Acids and Secondary Products of Thermally Degraded N-(1-Deoxy-d-ribulos-1-yl)-Glutathione

“…The calculated mass and measured mass of the RG-ARP in the positive mode were 440. 1333 12 The proposed molecular formula of the RG-ARP was C 15 H 25 O 10 N 3 S with a molecular mass of 439 Da by Mass Lynx software analysis (Figure 1a−c).…”

“…However, the varieties of flavor compounds derived from ARPs were far less than those from MRPs, which might be due to the asynchronous generation of recovered amino acids and α-dicarbonyl compounds from ARPs, and then limited the occurrence of Strecker degradation. 12,13 Some studies have shown that pyrazines could not be formed due to the release of recovered amino acids prior to α-dicarbonyl compounds in the ARP-only model, while the extra-added amino acids can compensate for the asynchrony and enhance the generation of pyrazines through Strecker degradation. 17,18 For the thermal processing of amino acid-derived ARPs, the influence of extra-added amino acids has been investigated and various improvements have been found for the formation of nitrogen-containing volatile compounds through Strecker degradation.…”

Formation Priority of Pyrazines and 2-Acetylthiazole Dependent on the Added Cysteine and Fragments of Deoxyosones during the Thermal Process of the Glycine–Ribose Amadori Compound

“…The concentrations of products derived from ARPs were found much higher than those from complete MRPs . When glutathione and xylose were used as raw materials for the preparation of ARPs and MRPs, respectively, it was found that ARPs could generate volatile flavor compounds more quickly during the heat treatment, and some new compounds such as 2-methyl-5-methylthio-furan and 2-furanmethanethiol could be formed compared to MRPs . These results confirmed the superior capacity of ARPs in aroma formation.…”

Key Aspects of Amadori Rearrangement Products as Future Food Additives

“…The glutathione-glucose system produced less roasted and nutty aroma with the same quantity as the glutamic acid-cysteine-glycine-glucose system, resulting from a slower release of hydrogen sulfide and ammonia participating in the subsequent volatile formation [ 70 ]. Glutathione-xylose-ARP was produced with a high yield of 67.98% by simultaneous dehydration reaction and produced more ketones, alcohols, and mainly furans (caramel-like and sweet flavor) than the mixture of the ARPs of the three amino acid constituents [ 30 , 71 ]. Additionally, the glutathione-xylose-ARP produced a few sulfur-containing compounds while the mixture of cysteine-xylose-ARP and three amino acid ARP mixture generated a potent meaty flavor, supporting the aforementioned suggestions that cysteine-xylose-ARP is capable of forming meaty flavors and the process is strengthened by glycine addition, possibly split from glycine-xylose-ARP.…”

“…HCAs are associated with tumor formation and cancers (breast, lung, stomach, and colon) in animal and human studies. [ 71 ] Formed by asparagine and reducing sugar, AA is linked with tumor formation and neurotoxic damage in animal studies [ 73 ]. Dietary consumption is mainly from Maillard-derived foods like fried potato, bakery, cereals, and coffee.…”